Pick My Brain is supported by our wonderful sponsors:

Founders scale faster on Deel. Set up payroll for any country in minutes, hire anyone anywhere, and get visas handled fast, so you stay focused on scaling. Deel takes care of onboarding, HR, IT, EOR, benefits, and compliance, so your team can grow without borders.

It’s why more than 40,000 fast-growing companies trust Deel to move fast.

Visit https://www.deel.com/dayone

Galah Cyber offers Application Security Assessment.

Get a clear, ten-minute snapshot of your AppSec maturity across the five core principles. Fast, practical insights you can act on straight away at https://www.galahcyber.com.au/assess

Episode Summary

Travellers can spend 15 hours over two months planning a holiday, then arrive with a messy spreadsheet, a graveyard of email confirmations and a screen full of Google Maps pins. Billy Chan and his co-founder built Alfred Travel to turn that fragmented process into a personalised, mobile itinerary travellers can edit, validate and book.

Alfred Travel had passed 1,300 users when Billy joined Pick My Brain. The company had closed a $250,000 pre-seed round and was preparing to raise $500,000 at a $5 million cap after reaching 15,000 users. Alan Jones puts on his investor hat to stress-test the story — and immediately finds the buzzword getting in its way.

They explore why “AI-powered” no longer earns points in a pitch, how Billy can teach investors something they do not already know about travel, and why a low-margin travel business has to think globally from day one. They also tackle geopolitical uncertainty, capital planning, affiliate economics and why Alfred’s proposed loyalty token belongs in horizon two, after the company has built meaningful scale.

Time Stamps

00:00 – The buzzwords investors are tired of hearing

00:59 – Welcome to Pick My Brain

01:51 – Meet Billy Chan and Alfred Travel

02:18 – From curious kid to technology founder

03:49 – The 15-hour holiday-planning problem

05:13 – How Alfred Travel makes money

05:40 – The founding team and a ten-year-old idea

07:01 – Why Alfred is a native mobile app

08:08 – Early traction and the ideal customer

09:24 – Personalisation without hallucinations

12:51 – Closing the booking loop

14:12 – The affiliate revenue problem

15:20 – The $500,000 seed-round plan

16:37 – Why “AI-powered” weakens the pitch

23:06 – Addressing global travel uncertainty

27:18 – Building a global company from day one

28:58 – Teach investors something they do not know

32:32 – Why this business cannot be cautious about growth

34:13 – Escaping the Australian launchpad mindset

36:57 – Loyalty tokens and the horizon-two trap

40:12 – Wrap-up

Resources

– Alfred Travel – https://www.alfredtravel.io/

– Billy Chan on LinkedIn – https://au.linkedin.com/in/billy-chan-4527818b

– Ask Alan a Question – https://speakpipe.com/pickmybrain

– More from Alan Jones – https://www.startupfoundercoach.com

About Pick My Brain

Pick My Brain is a Day One show hosted by startup founder coach and investor Alan Jones.

Mentioned in this episode:

Deel x PX_Script 1

Deel x PX_Script 2